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Another Top 10 Ugly Duckling Transformations in Movies

VO: Rebecca Brayton WRITTEN BY: Savannah Sher
These characters didn’t know their full potential until they got a makeover! For this list, we’re looking at even more great makeover scenes and character transformations in film. We’ve included characters like Marisa Ventura from Maid in Manhattan, Sam Montgomery from A Cinderella Story, Vivian Ward from “Pretty Woman”, Danielle de Barbarac from “Ever After” and more!

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Another Top 10 Ugly Duckling Transformations in Movies

This popular film trope definitely gives us enough content for a second list. Welcome to MsMojo and today we're counting down our picks for the Another Top 10 Ugly Duckling Transformations in Movies.

For this list, we’re looking at even more great makeover scenes and character transformations in film.

#10: Marisa Ventura

“Maid in Manhattan” (2002)

Jennifer Lopez stars in this modern day Cinderella story that is an amazing early aughts guilty pleasure. In “Maid in Manhattan”, Marisa Ventura works as a member of staff at the The Beresford Hotel and a case of mistaken identity causes her to strike up a romance with a wealthy man. We finally get to see her ditch the dowdy maids’ outfit at the end of the film when she gets all dolled up to attend a party. The fact that this scene is set to Diana Ross’ hit “I’m Coming Out” only makes it all the more fun.

#9: Sam Montgomery

“A Cinderella Story” (2004)

Hilary Duff does what she does best in “A Cinderella Story”: playing a totally awkward yet endearing teenager. In this rendition of the classic fairy tale, Sam wants to meet her online crush at a school dance but isn’t allowed to go by her evil stepmother. She goes anyway, with her help of her friends at the diner where she works, sporting an old wedding dress and a masquerade mask that somehow completely obscure her identity from everyone who knows her. Believable? Maybe not. But it’s magical nonetheless.

#8: Vivian Ward

“Pretty Woman” (1990)

Let’s be real, Julia Roberts is always gorgeous, but at the beginning of “Pretty Woman” when she’s in her street-walking get up and blonde wig, she definitely doesn’t look her best. In one of the most satisfying scenes from this classic rom com, we get to see her character Vivian go from underdressed to perfectly in style when she returns to that snobby Rodeo Drive shop to tell them what a huge mistake they’ve made. The shopping montage that takes place before, set to the song that gives the movie its name, is beloved for good reason.

#7: Danielle de Barbarac

“Ever After” (1998)

Another interpretation of the Cinderella story is this late ‘90s flick starring Drew Barrymore. Marketed as the supposedly real story behind the much-loved tale, “Ever After” introduces us to Danielle de Barbarac, whose father has died and who has long been mistreated by her stepmother and stepsisters. At the beginning of the film, she dresses like a common servant, but when the time comes for the big ball, she pulls out all the stops and looks absolutely ethereal in a white dress and pair of fairy wings.

#6: Jo Stockton

“Funny Face” (1957)

One of the greatest fashion movies of all time, “Funny Face” let audiences see Audrey Hepburn decked out in Givenchy for the duration of the film. The movie tells the story of an intellectual bookstore employee, Jo (played by Hepburn), who is discovered by a fashion photographer and brought to Paris to work on his new campaign. Jo is subtly elegant at the beginning of the film, but seeing her dressed up i the Parisian high fashions is pure eye candy that we just can’t get enough of.

#5: Annabelle Fritton

“St Trinian’s” (2007)

Annabelle doesn’t quite fit in at St Trinian’s, a school for wayward girls, because of her somewhat prissy attitude. So it comes as no surprise that her classmates kidnap her in the middle of the night to give her a new look that will fit the school’s aesthetic a little bit more. The audience gets to see each different clique trying out a makeover style for her, and the one they settle on is sexy, cute and a little bit edgy. Yes, Annabelle was beautiful before, but she’s got a lot more spunk after!

#4: Katie Simpson

“She's Out of Control” (1989)

When 15-year-old Katie’s father leaves on a business trip, her typical look involves coke-bottle glasses, braces, and frumpy clothing. When he gets back however, his girlfriend has helped Katie transform into a full beauty, who ends up causing trouble because she has all the boys in town in a frenzy. This movie may not have done well with the critics, with the legendary Roger Ebert particularly panning it, but we still love this transformation, even if Katie’s father doesn’t!

#3: Charlotte Vale

“Now, Voyager” (1942)

Bette Davis is one of the greatest iconic Hollywood stars, but you’d barely recognize her at the beginning of this 1942 film. She plays Charlotte Vale, an unattractive spinster who is abused by her mother; and, because of her emotional distress, looks about twice her age. After spending time away from her family home at a sanitarium, and then on a cruise, she manages to flourish, and returns . . . looking completely unrecognizable. Her eyebrows alone are a before and after that would be inspirational to anyone!

#2: Allison Reynolds

“The Breakfast Club” (1985)

One of the most iconic movies of the ‘80s also happens to feature one of the best makeovers in movie history. At the beginning of “The Breakfast Club”, Allison is the awkward and weird girl who is shown in sharp contrast to the pretty and popular Claire, played by Molly Ringwald. After spending their detention together though, the two girls bond and Claire gives Allison a completely transformative makeover. She may not quite look like herself, but it really does go to show what a little bit of makeup can do!

Before we unveil our top pick, here are a few honorable mentions.

Olive Penderghast

“Easy A” (2010)


“Gigi” (1958)

Janey Briggs

“Not Another Teen Movie” (2001)

#1: Fran

“Strictly Ballroom” (1992)

Baz Luhrmann’s amazing debut may not be as well known as its successors, but that doesn’t mean it should be overlooked. This charming film focuses on the Australian ballroom dancing world, and in a plot somewhat similar to the classic “Dirty Dancing”, an experienced male dancer finds himself taking on a raw beginner to be his partner. Fran is the “Baby” of this story, and when we first meet her she’s one of the most awkward characters to ever grace our screens. By the end of the film though, she really comes into her own, and shows an elegance and poise we never could have imagined.


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